It sounds like you're agonizing over past decisions. Been there, done that! We're all human and have to make choices with imperfect information. Sometimes we p

It sounds like you're agonizing over past decisions. Been there, done that! We're all human and have to make choices with imperfect information. Sometimes we pick the right choice, sometimes we don't. All you can do is learn from it, and this helps you inform your future choices, e.g. we get a bit wiser in the process. Figure out what your goals are - if you really want a management role, then figure out how you can get there from now and start taking steps towards it. It might be studying an MBA part time for example. Or getting involved in leadership activities, like being on your local HOA board, school board, or similar. Ask your manager what steps you can take to move into a management role. Follow the philosophy of "act like the role you want" and you may get noticed as having leadership / mgmt potential. Beyond that, if you are agonizing over the past like it sounds like, there may be underlying emotional issues you need to sort out with a professional. Like for me, I have struggled life long with intense self criticism and over analysis of everything I've done. Like agonizing for weeks/months over a decision, something I said, etc. and beating myself up over it. That kind of thinking process _is_ pathological and a professional can help.